Q: Outlook for Mac 2011 on OS X 10.11 hangs during account sync operation

From the sounds of silence, I'm guessing i'm up the proverbial creek w/o a paddle as far as Outlook goes.  Guess I will go back to the original hanging identity and try deleting the gmail account that appears to be causing the hang and if that doesn't do it, the next option appears to be ditching Outlook for Apple mail.  In retrospect, I probably should have switched over as soon as Apple mail started having good support for Exchange, especially after hearing other Outlook horror stories, but having not had any real difficulties with Outlook Mac or Entourage (outside of lack of compatibility with Windows Outlook) previously I stayed the course with Outlook with the hope of better compatibility with Windows Outlook. 

Even the eval version of "Stellar Phoenix OLM Repair" hangs on my .olm file <sigh>

Anyone have any other thoughts available on how to get back to where I was before this happened?

Restore the Microsoft Office directory to before the 14.6 update?  1/12/16??

I would do an export as individual items. It's possible the problem is in only one type of data...usually messages.

File > Export select  one item at a time. Save Mail to  the last. Before wasting your time exporting Mail, try importing contacts, calendars, notes and tasks.olm files into your Identity. If they don't crash Outlook, you can try Mail, but create a separate Identity for testing the import. Don't want to mess up what you have already imported.

Note: if you get a log file with the .olm file, this means not everything exported. The log file doesn't show up instantly so give it a few minutes.

Yes, I would start over in a new Identity. Since the new Identity really doesn't contain any data, it's not much of a loss.

You can try Emailchemy to recover your messages if the export as .olm file fails. Select the export as .mbox file. That way you can see the individual folders. You'll know exactly what exported. The demo will put a watermark on your messages but you can try it first to see if it's success or if the Identity is too corrupt to export. After you export as .mbox file you can then select to convert just the local "On My Computer" mbox files to .rge (this is the same as .olm for Outlook 2011). Outlook makes you import each .mbox file one at a time. Converting to .olm will give you the one file to import. Note: Apple Mail can import all mbox files with one import. This keeps your folder structure.

Emailchemy

Has a demo you can try first. $29.95

http://www.weirdkid.com/products/emailchemy/

Yes, i did get a log file, looking within there were 4 attachments it was unable to write, then this "Error exporting folder 'On My Computer/Inbox'" followed by a  bunch of old calendar events that had no master... could care less about them as they are all old.  Most of my calendar events are from the Exchange account now.  For the original default account (ISP email address) I really don't care about those attachments either.  The only thing I really care about (and it isn't a terribly high priority) is the mail and there are possibly some contacts in there...

Will try exporting separately and see what that does...  My Exchange is good, anything not currently on the server is already archived in FileMaker, ditto for the main gmail account.  The other gmail account is one i use for junk mail primarily but there are a few items in there that may be worth keeping.

You can delete any IMAP and Exchange accounts before trying to export. this would leave only "On My Computer" data. Work off a copy of your Identity!!

The only thing I really care about (and it isn't a terribly high priority) is the mail and there are possibly some contacts in there...

If you are hoping to recover the the hidden autofil contacts, these do not export. However, they are saved in Data Records folder. Look for Recent Addresses.

You can create a new Identity and drag over the folder "Recent Addresses" then rebuild the Identity. I would duplicate this in case you need it for further testing. Import your .olm files into an Identity that has the recent addresses.

Autofil , Autocomplete or Most Recently Used (MRU)

These entries are not in the AddressBook.

AutoComplete feature gathers addresses from both the address book and the recently-used list (with a maximum of 200 entries). They are sorted intelligently, organized by the frequency of messaging for each contact, with the most-used contacts showing up on top.

There will always be 200. Some will always be considered "useless" by the user. The better organized you are at adding "good" addresses to you address book the more you will enjoy the MRU feature.

Don't rely on this list as a substitute for adding contacts to the AddressBook.

So far so good!  Thanks for the help!  Only had mail and calendar items to export/import, but that brings up another issue I've noticed (and am seeing as I type this) calendar items, especially US holidays etc, that add multiple copies of the same event.  Have you seen this and do you know of a way to get it to stop and get rid of the extras?  In fact they are duplicating like mad right in front of my eyes.  I now have over 1600 of ONE CALENDAR item and growing w/o stopping

The replicating calendar items are going like crazy!  Previously they had just been holidays etc that replicated on the wrong day (usually a day before) and on the correct day and I'd have say 6-10 (possibly more) of the same item for each one.  Right now, an old appointment from 2011 is replicating crazily!! I already deleted over 2600 of them and they are still growing (this is within the search screen you show in your instructions for moving over calendar items after the import.  But the holiday on wrong day & correct day plus extra of each item had been going on previously and seems to be still within the imported calendar

Just had to delete the entire imported calendar because many of the entries were multiplying like crazy.  Some calendar items will come with my Exchange account, but many of the personal ones won't come back w/o this imported calendar.  It has been an issue before (as mentioned previoiusly), but I've NEVER seen it do this before!!

In the Identity with multiple holiday events...

Under Organize in the Outlook toolbar, select List.

2) Click in the top search box. (you do not have to enter anything)

3) Select All Events

4) Click on Advanced

5) Set criteria to Category is Holiday (you might have other Holidays categories)

6) Click on + to add all holiday categories you have.

7) When search completes, select all then delete.

Note: there is an option under File > Import to import holidays.

Thanks!  I knew about importing holidays, that's how i got them initially, now I'm reluctant to do it again because it seemed like that is where this crazy replication started in the first place. The latest problem is that even entries I created started multiplying infinitely!  I had to delete the whole imported calendar to get it to stop.  Fortunately I had not yet had  a chance to move the calendar entries over to the local structure (but there was no way I could have anyway, things were replicating like crazy right in front of my eyes)  For one event, I selected over 2600 events to delete and there were more below it replicating even before I could delete the first batch.

It also seems like i went through the process of deleting/reimporting all of the holidays only to have the replication show up again.  Since it has been happening to events I created or accepted as well, now it seems like it must be something other than just a holiday issue.

Thank you again for the EXCELLENT help!  I will definitely keep your site at the ready and direct anyone I know with Mac Office issues to it as well!

You have to remove holidays from old Identity then create a new .olm file for calendar.

Import into a new Identity. Sorry, I know this sounds like a bad echo.

Don’t import holidays until you get your calendar events imported correctly.

Make a duplicate of the Identity, then add holidays. If there is a problem, you can revert to the copy.

Yep, yep, and yep!    No worries, once I figured that it was something in the old calendar, I went back to that identity and did the painstakingly tedious task of removing ALL holidays (many of which were did not have ANY category) , and then year by year every replicated event.  Finally was able to remove all but a handful of events I had created which wanted to send cancellations but would never remove themselves even after cancelled.  Since there were just a few and they were from years ago, I just left them, exported the calendar individually to a .olm file, opened Outlook again under the newly created and clean identity, and imported the cleaned up calendar .olm file.  Now I have a clean identity and will create a backup of that before I start adding the Gmail and Exchange accounts.

Anything else you recommend I do before adding the Gmail and Exchange?

My apologies for the SHOUTING IN ALL CAPS, BUT THANK YOU, THANK YOU, THANK YOU!!!  I may have eventually come up with some of this, but for the VAST majority of it, your expertise was an EXTREME TIMESAVER!!  Also greatly benefitted from the techniques and outlined steps you have on your site.  Your site will be a goto site for me for any additional Mac Office issues that I'm sure will arise...

Identity is completely rebuilt and all, email accounts are added back, and all IMAP and Exchange mail appears to be resynced.  The problem now is that Outlook is crashing every few minutes, sometimes I get the crash where it wants to notify Microsoft, but most of the time it is just the one where it says "Microsoft Outlook must be closed because an error occurred. Any unsaved work may be lost."  This literally happens every few minutes or less and I'm not sure how to get rid of it...  With the added Exchange functionality now in Apple mail, I'm beginning to wonder if Outlook is even worth the hassle...  Up until last week, multiple days of it running without issues after the 14.6 update, I had been relatively issue free with Outlook.  Now it won't stay running for more than just few minutes at a time.  It always seems to come back up without any errors, it just crashes again within a few minutes.

Is it likely that this is related to the sync hang and subsequent identity rebuild?  It had been running fine up until the sync hanging issue in 14.6 that earlier this week...  (it just _seems_ like a LOT more time has lapsed since then)

Have you rebuilt the current Identity?

Are you getting an error message? Is it going to Microsoft or Apple?

Identity has been completely rebuilt (as per our previous discussions).  The error is going to Microsoft when it gets that far.  Most of the time just tells me it needs to quit and I click the quit button and restart Outlook.  The "Send to Microsoft" seems to come up when I leave the computer for a while and the "... you must quit..." type message pops up, but I have not been there to respond immediately. 

As of today, the crashes have been farther apart, so I don't know maybe it is was just getting resource starved due to trying to sync all of the gmail IMAP messages???  It still hasn't caught all the way up on one account...

As far as error messages I get this most of the time: "Microsoft Outlook must be closed because an error occurred. Any unsaved work may be lost."

If that has been sitting for some period of time, I will also get a message requesting to send the info to Microsoft and it will auto restart Outlook.